


The Christmas Diaries

by SorenMarie



Category: Supernatural
Genre: 25 Days of Christmas Prompts, Candy Canes, Christmas Proposals, F/M, Fake/Pretend Relationship, Friends to Lovers, Grace just wants another sibling, Hot Chocolate and Chill, Innuendo, Meddling Sam, Warm and Fuzzy Feelings, Winter wedding, hunting loss
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2019-02-12
Packaged: 2019-09-06 12:02:21
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 25
Words: 13,980
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16832242
Author URL: https://archiveofourown.org/users/SorenMarie/pseuds/SorenMarie
Summary: A story spanning over 25 different prompts involving your growing relationship with Dean.





	1. I’m never taking this off

You and Dean had a bet going. **  
**

The loser would have to spend the whole day in an ugly sweater of the winner’s choosing. You wanted to win. In fact, you had the sweater hanging up in your closet at the bunker.

You stumbled on it by chance when you were doing a supply run, but you knew if you didn’t pick up right then and there, it’d be gone.

“So how many does that make?”

“Let’s see this nest had a houseful of vamps but if I had to stop and count, I’d say it was over 20.”

“And how many of those did you kill?” You rolled your eyes when you realized Dean was gloating. “I think, if I remember the terms of our bet - you have to spend the day in an ugly sweater.”

“I remember! Thank you very much.” You grumbled as the two of you made it back to the Impala. Dean chuckled as you opened the passenger door and climbed in. 

–

“Dean, I thought this was supposed to be an ugly sweater!” You called out from down the hall. You were wearing a pair of black tights, a black skirt, and a red sweater with the words ‘Sleigh my name’ in white. It made you chuckle when you slipped it on but you were surprised that it was so comfy. Maybe losing this bet wasn’t such a bad thing.

“Holy shit Y/N.” Dean muttered as you walked by. “Nope, no fair you obviously cheated.”

“I did not cheat…” You felt a smile form on your face as you looked over at Dean. “I do however have a sweater in my closet for you if you wanna join me.”

Dean’s raised eyebrow made you chuckle as he darted down the hallway to your room. You waited for a few minutes before he returned wearing the ugly Batman sweater. “I’m never taking this off.” 

“It has to be washed sometime Dean…” You unlocked your phone and brought up your camera app. “Come here, you big dork. Take a picture with me.” You felt Dean place his arm around your waist and your cheeks turned pink. After a couple of tries, you got the picture you wanted. Dean wandered into the kitchen as you took a seat in the war room. 

“Hey, send me that will you?” You jumped when you heard his voice appear out of nowhere.

“I swear, I’m going to put a bell on you.” You muttered to yourself as you sent Dean the picture. 


	2. I’m tired of the two of you dancing around each other.

**Summary for the Chapter:**

> Who hung up all this mistletoe?

The boys didn’t share your enthusiasm for the holidays, so the only room that was decorated for Christmas was yours. You had a small green and teal tinsel tree with purple, pink, and silver ornaments on your desk and instead of using your normal lamp, you put up Christmas lights. **  
**

There was just one thing bothering you. No matter where you went in the bunker, mistletoe was hanging up. 

You made your way to the kitchen where Dean was pouring himself another cup of coffee and was watching the stove carefully. “I have to ask, who hung up the mistletoe?” Dean quietly sighed as he turned to look at you. “It wasn’t me, I swear. The only room I’ve decorated was my own.”

“This is one shitty start to a prank war if it was who I’m thinking of.” You started to respond when you felt your phone go off. _Just kiss him already! I’m tired of the two of you dancing around each other._

Dean’s phone went off at the same time and he rolled eyes as he read the text his brother sent. “Let me guess Sam?”

“Yeah. Look, I get what game Sam is playing but it won’t be like this. Our first kiss will be special.” He winked at you and pushed a plate with a bacon cheeseburger and some fries towards you. You turned your head quickly and muttered a faint thank you.

You heard Dean chuckle as you took a bite of the burger in front of you. He took a seat across from you and the two of you ate in peace.

Your first kiss happened later that night while the two of you watched Die Hard.


	3. Take the damn jacket.

**Summary for the Chapter:**

> Something goes wrong with the furnace

“Take the damn jacket, Y/N.” Dean was holding it out with one hand. Your hand brushed his as you grabbed it, shedding your blanket cape off. Your teeth chattered as you slipped into Dean’s jacket. “Your hands are freezing!”

“Why’s the heat out anyways?”

Dean raked his hands across his face with a sigh. “I have no idea… “ He threw the wrench he held in his hand off to the side. “Come on, let’s get you warmed up.” He took your hands into his and gently rubbed them, hoping that would warm your hands up.

Sam watched the two of you walk away with a shit eating grin on his face. “I knew it.” He carefully picked up the wrench and put it back into the toolbox. Sam pulled out a Phillips head screwdriver and he made sure to put the part he removed earlier back into the right spot. 

He found the two of you asleep in Dean’s room under your blanket. 


	4. Come pick me up

**Summary for the Chapter:**

> You need to get out of the bunker for a little while.

You were bored and despite what both of the boys told you, you needed out of the bunker. You were going stir crazy with nothing to do. So you figured a nice drive would do the trick. Maybe you’d go and see how the residents of Lebanon were decorating their houses. **  
**

It was a good idea at the time. 

Your car broke down just as the sun was setting. You managed to pull off to the side of the road and put the car in park.

It was too dark to check your engine to see what was wrong so you groaned. Something caught your attention however, there was a yard across the way that was decked out in decorations. Your eyes widened as you took everything in and snapped a few pictures. “Well here goes nothing.” You muttered to yourself before pulling Dean’s name up on your contact list. You were about to press the button to call when your phone started ringing.

“WHERE THE HELL ARE YOU?” 

“Right now? Broke down in front of some farmhouse. I had to get out for a little bit.”

“Something could’ve happened to you and I -” Dean paused and you heard him ask Sam to track your GPS. “Y/N, I need you to keep talking…”

“I’m sorry for taking off like that.”

“We could’ve gone together - I’m guessing you drove around looking at the lights?”  
  
“There were some pretty good displays. People really put their all into doing this.” You realized after you answered what Dean had said. “Wait, Dean, do you mean that?”

Dean was trying to play it off like he wasn’t interested but it was something that always put a smile on your face. It always made him happy whenever you felt happy. “Yes.”

“Come pick me up and we’ll watch some movies in my room with the Christmas lights on.” 

“You got it. Y/N? I’m glad you’re safe.” You heard the dial tone and realized Dean hung up. You felt your cheeks heat up as you looked at the background picture of your phone. It was the picture you took the other day with Dean in your sweaters. You had it bad.


	5. Mom, what’s wrong?

**Summary for the Chapter:**

> This one is a flashback

**Notes for the Chapter:**

> Day 5 - Decorations

You always had a huge grin on your face whenever your mom pulled out the red and green totes from the attic. She would let you and your sister help out, but when it came to decorating the tree, you always had to wait until your father got home from work. 

Only this year, your mom went with him. 

“Sis?” Your younger sister Harley appeared in the doorway with her pet hedgehog Jeffrey in hand. “Are mom and dad back yet?”  
  
You paused the movie you were watching as she came to take a seat next to you on the couch. “I haven’t heard from either of them.” 

“I’m getting worried. What if something bad got them?” You had the same suspicion in the back of your mind but you shook your head. The both of you looked at each other when the phone in the kitchen started ringing. 

“Harley, do you remember where our emergency bags are?” 

“Aren’t they in the hallway closet?” 

“Yeah. It should our bags and a special bag mom and dad packed for us in case.”

“Want me to put them by the door?”

“Yeah.” The answering machine kicked on and you froze. 

“Girls, you don’t know me or have any reason to trust me but I do know your parents. They ran into some trouble and sort of entrusted me to come and get you.” 

“Is that Uncle Bobby?” You opened the living room curtains and there was a 1971 Chevelle sitting outside where your dad usually parked. 

“It is. He’s telling the truth. Do you have Jeffrey’s cage?” Harley nodded as you helped get her shoes and coat on. You made sure to turn out the lights and locked the door as the two of you made your way towards Bobby’s car. 

\--

The car ride to Bobby’s took about half an hour. Harley was resting on your shoulder as Bobby pulled up to his house. “Harley, hey we’re here…” You helped her out of the car and Bobby took your bags inside and your mom rushed outside and hugged the two of you tightly. “Mom, what’s wrong?”

“They…” Her lips trembled and she wiped away tears that threatened to fall. “they got daddy.”

“No!”

“What exactly got him?” You quietly asked as your mom rubbed Harley’s back. You heard her sigh before she answered. 

“I don’t know exactly.” She answered quietly.

\-- 

You had been at Bobby’s for a week now and you were currently sitting outside with your sister when the two of you watched a black car pull up. The two of you watched as an older gentleman got out and his two sons followed behind. They occasionally glanced over at the two of you, and then you heard yelling. 

“I wonder what’s going on.” You muttered as you put the finishing touches on a tiny santa hat for Jeffrey. 

“It’s none of our business Y/N.” 

“Party pooper.” 

“Girls, come on! Go get your stuff, we have work to do!”

“Yes momma!” 


	6. Hot Chocolate and Chill

**Summary for the Chapter:**

> When you have trouble sleeping, you make something that your dad taught you.

**Notes for the Chapter:**

> Day 6 "I happen to make very good hot chocolate.”

Not many people knew this but your father was the one who taught you how to make hot chocolate. He’d always ask if you wanted to help him out, and every time you said yes. The whole process didn’t take that long but you always loved spending time with him. After he passed away however, you’d find yourself in the kitchen crying. He taught you everything important, and yet some monster took him away from you, your mom and your sister. 

You knew it was coming up - the anniversary of your father’s death. You zoned out while you were watching a Christmas movie, so you paused it with a sigh. With a big yawn, you threw your legs over the side of the bed and put your slippers on before leaving your room. 

The noises coming from the bunker Dean could deal with. He had gotten used to them over time. He was coming from the bathroom when he first got a whiff of something sweet. Once he figured out what it was, the smell of chocolate brought Dean to the kitchen. He watched you from the doorway in his grey dead guy’s robe. You were humming to yourself as you carefully poured the hot liquid into one of your novelty mugs.

“Having trouble sleeping?”

“A little bit.” You blew on your coffee cup before taking a sip. You placed it back on the counter while Dean pulled a stool closer and took a seat. You quietly chuckled as you pulled an empty mug down and looked over your shoulder at him. “You want a cup? I happen to make very good hot chocolate.”

You handed him your cup and nodded, giving Dean permission to take a drink from your cup. He carefully took a sip and and hummed in approval. You carefully poured another cup as Sam wandered in with a strange look on his face.

“Whatcha two up to?” 

“Can’t sleep.”

“Heard a weird noise so I came to investigate. Turns out it was just Y/N.” As you watched Dean take another drink, Sam watched the two of you. 

“Y/N, I know this is probably the last thing on your mind right now but Dean is drinking from your cup.” You shrugged but you watched as a grin formed on Sam’s face. “You do realize that’s an indirect kiss, right?”

“What’s your point Sam? It’s not like I haven’t kissed your brother.” Dean’s face flushed as Sam’s grin grew wider.

“All I need to know right now is do I need to wear my headphones tonight?”

“Why would you need to do that?”

“As much as I love the both of you, I don’t need to hear what happens during your hot chocolate and chill time.” Sam practically sprinted out of the kitchen cackling. Your face was on fire and when you looked over at Dean, his was no better. 

“Why is your brother such a pain in the ass?” You muttered.

“I’ve been asking that for awhile now.”


	7. I’m sorry we can’t spend the holidays together.

**Summary for the Chapter:**

> Instead of spending the holidays with the boys like you want, your mom needs your help on a hunt.

**Notes for the Chapter:**

> Day 7

You were eating breakfast in the kitchen when your text tone went off. “Mom really?” Sighing, you took another bite before replying. You were in the middle of typing out your response when your phone went off again. This time it was your sister. She was asking if you replied to your mom yet and you told her not yet. **  
**

You were typing furiously on your phone when Dean wandered into the kitchen. 

“Hey Y/N, something wrong?” 

“My mom wants me to come help her on a hunt. I don’t know how I would even meet her since my car died..”

“You could always take one from the garage. There’s plenty to choose from.”

“Aww here I was hoping that I could take Baby.” He narrowed his eyes and placed the coffee cup he was holding on the table in front of him.

“Y/N, look I like you and everything, but no one drives Baby.” You squeezed his hand gently with a wink and grinned.

“I know. I was joking.” Sam glanced over his laptop screen at the two of you. He was quietly watching what was going on. “Guess I need to go pack, and maybe you can help me pick out which car I can take?” You placed your bowl and cup in the sink and kissed Dean’s cheek on the way out. Once he knew you were out of sight, he glared at Sam.

“I know you want to say something..”

“You two are adorable. That’s all.” Sam carefully closed his laptop and stood up.

–

You were halfway to the garage when you heard someone approaching from behind. Your world went dark, but you smiled when you realized it was Dean who had placed his hands over your eyes. “I was going to save this for Christmas but there’s something I want you to have.” The two of you marched slowly down the hallway. Dean removed his hands but told you to keep your eyes closed. 

“Come on Dean!”

“Just one second.” He pulled out a set of keys and placed them in your hands. He watched you feel the ridges of the key in confusion. “Go ahead, open them.”

Your eyes fluttered open as you looked over at the ‘67 Ford Mustang with two orange racing stripes. “What the hell, Dean… You didn’t.”

“I know Bobby’s Chevelle meant a lot to you.” You wrapped your arms around Dean with the biggest grin on your face and he smiled. “I know you’ll be safe in her because she’s Baby 2.0”

“No one could ever take the place of Baby, you know that.” You stood on your tiptoes and gently kissed Dean. 

“I - what - Y/N?” You pulled away from Dean flushed and opened the car door. Dean watched in stunned silence as your new car roared to life. 

“Hey Dean?”

“What’s wrong?”

“I’m sorry that we can’t spend the holidays together. I really wanted our first Christmas together to be special..” 

“Hey, there’s no need for that. We’ll figure something out, I promise.” 

–

Two weeks. That’s how long you were gone. One hunt turned into two but you didn’t mind spending time with your mom and sister. You missed Dean even though the two of you had been texting back and forth since you left. 

“Hey kiddo, Harley and I are gonna take off.” Your mom pulled you in for a hug with a grin. She pulled away and Harley took her place.

“Already?”

“Yeah, nothing beats sleeping in your own bed and these hotel showers have the worst water pressure.” You chuckled and Harley looked at you with a confused look on her face.

“Dean says the same thing.”

“Mom look, she’s blushing.”

“Shut up! You’ll meet him one day, I promise.”

–

You were watching The Year Without A Santa Claus on tv when your stomach started growling. “I know I should get something to eat… but I don’t want to leave.” You were looking up local pizza places when your phone went off. 

What room are you in?

24, why?

Just answer your door, please? It’s freezing out here.

“You’ve got to be kidding me.” Muttering to yourself, you made your way over to the door and glanced through the peephole. Carefully unlocking the door, you opened it far enough so that both boys could slide through.

“I’m excited to see you guys, don’t get me wrong but why?”

“Someone - not mentioning any names was getting worried about you.” You heard Dean mutter in the background and you smiled at the exchange. Sam put both boxes of pizza on the table, and started rustling around in another bag. He pulled out a small novelty Christmas tree, and a few wrapped presents. 

“You guys didn’t have to do this.”

“I know how excited you were to spend Christmas with us.”

“Y/N, whether you like it or not, you’re family. Just can I ask a favor?”

“What?”

“Give it a year or two before making me an uncle.”


	8. Please tell me Sam didn’t give you a drink

**Summary for the Chapter:**

> Sam hands you a drink meant for Dean.

**Notes for the Chapter:**

> Sam being himself. Language. Mentions of vomiting

“Please tell me Sam didn’t give you a drink.” He watched you take a big gulp and grimace. You passed your cup off to Dean who sniffed the cup cautiously. “Son of a bitch. SAM!”

“What?” He appeared around the corner and stopped. “She didn’t -” You held your hand up to your mouth and took off like a bat out of hell. Dean heard you vomit in the hallway, and he cringed. Someone would have to clean that up later, but for now he wanted to make sure you were okay. “That was meant for you Dean, not her!”

“Hey, it was accident. Don’t beat yourself up over it.” Dean placed his hand on Sam’s shoulder with a slight grin. “She’ll forgive you, I’m pretty sure of it.”

“Go take care of your girlfriend.” Sam rolled his eyes as took a seat at the war table with his laptop. 


	9. We could always start a new tradition

**Summary for the Chapter:**

> Your snowed in so you and the boys spend time watching a familiar Christmas special

“You know in Germany, they have a pickle ornament that they hide somewhere in the tree and children have to find it for an extra gift from Santa.”

“Dean, have you played hide the pickle with Y/N yet?”

“I hate you so much.”

“You love me and you know it!”

You rolled your eyes as Dean handed you a plate with a couple pieces of pizza on them. This wasn’t exactly how you wanted to spend the holidays but the three of you were currently snowed in with nothing to do. While the boys were talking, you were flipping through the channels when you stopped on The Year Without A Santa Claus and you smiled.

“Dean, look!” You took a bite of your pizza as Dean took a seat next to on the bed. You were mouthing along to one of the songs when you heard Dean chuckle beside you. “What?”

“Nothing, you’re adorable that’s all.”

“Shut up.” You felt your face heat up and Dean laughed again.

“So Y/N, what was Christmas like where you grew up?” Sam asked as a commercial came on.

“We’d always wait until after Thanksgiving to put the tree up but everyone helped. My mom and sister are allergic to pine trees so ours was always fake - but it didn’t matter. We had our own ornaments and we’d all decorate the tree. Harley and I took turns putting the star up on the top of the tree with dad’s help.” You smiled at a random memory that popped up in your head. “We’d watch a Christmas movie every night with hot chocolate. We did that until dad passed away.” 

“We could always start a new tradition..”

“I thought we did that last year - The Year Without A Santa Claus and pizza.” 

“You do know we could change it up right? There are more Christmas specials out there.”

“Not to mention movies…” Dean chimed in and you chuckled. You unlocked your tablet and pulled up a folder of Christmas movies.

“So what do you want to watch first A Christmas Story or National Lampoon’s Christmas Vacation?” 


	10. Can I get a pet like Aunt Harley?

**Notes for the Chapter:**

> This one is a few years in the future but Grace Winchester will be a thing ;)

“Uncle Sam, what’d mommy mean when she told daddy he’d look good in a Santa hat?” Sam leaned over and held his hand up as he whispered into your daughter’s ear. You watched as her face scrunched up in disgust as she looked over at you at Dean. **  
**

“Samuel Winchester, I swear to Chuck if you told her anything…”

“Why are you being so mean to Uncle Sam? He didn’t do anything wrong!”

“Gracey, look at me, okay?” As soon as those green eyes met yours, you knew she had you. “We’re only teasing Uncle Sammy, okay?”

She sniffled as she looked up at her uncle who was sitting next to her. “Are they telling the truth?”

“They are.”

“Uncle Sammy’s feelin’s aren’t hurt?” 

“Of course not.” He winked at the younger girl and you heard Grace giggle. You chuckled as you opened the stove door to check on the batch of cookies you were currently making.

“Mommy?”

“Yes my angel?”

“Can I get a pet like Aunt Harley?” You glared over at Sam who shrugged his shoulders and was trying hard not to laugh. 


	11. He's wishing it was him

**Summary for the Chapter:**

> Dean's watching you innocently eat a candy cane

**Notes for the Chapter:**

> Trust me - the other story I talked about in the beginning will get released one day lol

Dean was watching you from across the table. He was nervous at first when you pulled the lone candy cane out of your bag. The last time there were candy canes in the bunker, it resulted in a trip to the hospital and one grumpy Dean. You carefully unwrapped the bottom and pushed the plastic down. You didn’t hear Dean gulp as you took your first lick. 

“Dude, stop being creepy.” Sam’s voice rang out and made him turn around in his chair.

“What?” You bit of a small piece that was getting too sharp and Dean coughed. “Am I doing something wrong?”

“Dean’s just wishing he was that candy cane at the moment.”

“Damn it, Sam.”

“It’s not my fault you can’t get your girlfriend to tickle your pickle.”

“You didn’t just say that.” You were laughing so hard that you started coughing that both of the boys looked over at you in concern. 

“Just say the word Sam, I have a few friends that would love to tickle your pickle.”

“I wasn’t aware you had any friends.” 

“Ouch, Samuel…”


	12. Mommy, will I be on the naughty list for this?

**Summary for the Chapter:**

> Your daughter has the same love for pie that Dean does.

**Notes for the Chapter:**

> Day 12 - “What if I’m on the naughty list? Do I get anything?”

You were curled up next to Dean on the couch deciding what to watch next when you heard noises coming from somewhere in the bunker. Sam and Cas were in their rooms, and Grace was asleep.

“Dean, what was that?”

“I don’t know. We’ll leave it alone for now and check it out later.” Dean wrapped his arm around your shoulder and pressed a soft kiss to your forehead before changing the channel. The two of you sat there watching some Western on tv and you felt yourself nodding off. It wasn’t until you heard multiple things falling that you shot up and ran towards the noise with Dean trailing behind you. 

“Grace Winchester, what in the hell do you think you’re doing?” There were a few pie pans on the floor upside down with the contents spilling out. 

“Y/N, please tell me this can be salvaged. Please?” Grace was slowly backing out of the room while you and Dean were distracted. “I don’t think so missy, you get back here and clean up your mess.”

“Yes sir.” You sighed as your daughter started picking up the pans she dropped and placed them on the counter she could reach. Dean’s expression softened as he went over to help.

“Grace, you could’ve just asked if you wanted another slice of pie. Why the sneaking around?” You asked softly.

“I was afraid you’d say no. I mean daddy always gets seconds and thirds, so why can’t I?”

“Daddy is obsessed with pie, ask anyone.”

“Hey!”

“What, it’s the truth.” You heard Grace snort in laughter and that made you laugh. Dean huffed as the three of you worked towards cleaning up the kitchen.

“Mommy, will I be on the naughty list for this?” Grace looked over at you with a frown.

“I think you’ll be safe as long as you don’t do something like this again.” 

“I’ll be a good girl, I promise.” You heard her mutter to herself as she left the kitchen. Dean gave you a brief hug before following after her, and you sighed.   
  
The amount of pies you managed to make during the holiday seasons doubled once Grace was born. It started before Thanksgiving and lasted way past Christmas. You knew you’d have to replace the pies that were ruined tonight but you’d wait until tomorrow. You smiled and knew that if you asked Grace to be your helper, she’d love it. 

–

“Grace is down for the count but there’s something I have to ask.” You hummed in response as Dean closed the bedroom door and made his way over to the bed. “What if I’m on the naughty list? Do I get anything?”

“A swift kick in the ass, I don’t know.” You winked at him playfully and Dean grabbed a hold of your ankles, pulling you closer to the edge of the bed. He leaned over you as your face flushed and Dean chuckled. “If you’re a good boy, I’m sure I can think of something that will get you off of the naughty list.”


	13. It’s not polite to keep a lady waiting

**Summary for the Chapter:**

> You have one last thing to do before you finish decorating the tree. However your daughter and Sam have hidden the ladders.

**Notes for the Chapter:**

> Day 13 - “I can’t reach the top of the tree.”

“Jingle bell, jingle bell, jingle rock.” You were singing along to the playlist you and Grace put together as you wrapped garland around the lower branches of the tree. You took a step back to admire your work when you felt a large hand crack you in the ass. “Dean Winchester, I swear to god, I will end you if you do that again.” **  
**

“How’d you know it was me?” You didn’t have to turn and face him to know he had a smirk on his face. You rolled your eyes and smacked him in the shoulder. “I thought Gracey would be in here helping you.”

“She was but your brother bribed her away.” 

“Need some help?” He shook the empty box of ornaments he picked up with a grin and you shook your head. The tree was done but you were holding the star tree topper in your hands with a frown on your face.

“This is the last thing that needs to go up and I can’t reach the top of the tree.”

“Why don’t you use the ladder that’s in the supply closet?” You kissed your middle finger and blew it towards Dean as you left the room. You heard him chuckle as you stepped out of the war room and made your way towards the supply closet. Opening the door slowly, you flipped on the light and stepped in. You searched everywhere you could think of but you couldn’t find it. You flipped the light back off and made your way back. 

“Dean, the ladder is gone.”

“I put it back after I used it the other day. Wait here..” Dean left and returned with a frown on his face. “I swear I put it back.”

“Babe, it’s fine. We can figure this out.” Dean turned around so that his back was facing you and lowered himself to the ground. You watched with a raised eyebrow and giggled when he turned around and asked you to get on his shoulders. “You’re kidding right? Dean no, I’m too heavy!”

“Get your ass on these shoulders now.” 

“Fine.” 

–

With Dean’s help, you were able to finish the tree in no time. “Hey Dean, is there a reason there’s mistletoe above the tree?”

“You know how Sammy is. He’s probably still bitter about hanging all that mistletoe years ago and we never kissed under it.” There was something more that Dean wasn’t saying so you shrugged it off. “Are you sure it’s just mistletoe up there and nothing else?” He was worried that Sam and Grace screwed up earlier.

“What are you talking…about.” You didn’t notice it at first but there was a silver band with a star shaped diamond in the middle being held up by a red ribbon. “Dean, you didn’t…did you?”

You could feel him feel him chuckle as you attempted to untie it. “I did. So, what’s your answer?”

“Can you let me down first?” He helped you get down from his shoulders as you held the ring in the palm of your hand. 

“It’s not polite to keep a lady waiting Y/N.” You chuckled as you handed Dean the ring with a smile on your face. “Is that a yes? SAMMY, GRACEY, SHE SAID YES!” You watched him slide the ring on to your finger and twirl you around. You kissed him gently and from the doorway you heard both Grace and Sam pretending to throw up. The two of you chuckled and kissed again. 


	14. Can we go caroling?

**Summary for the Chapter:**

> Grace asks if you can go caroling

**Notes for the Chapter:**

> Day 14 - Christmas Carols

You were going to murder your brother-in-law. 

Sam had offered to babysit Grace while you and Dean did some Christmas shopping. It was an easy enough job. Or at least you thought it was.

“Mommy, daddy, can we go caroling?” Grace had asked the two of you once you had everything put away and were relaxing together on the couch. 

“Babygirl, no one really does that anymore.” You heard Dean snicker and you jabbed his side. “You have something to say Winchester?”

“I recall your mom telling me some stories when you were younger that involved you and your sister dressing up as carolers. I believe she had the pictures to go with it.”

“I hate you.”

“You love me, that’s why you agreed to marry me.” You waved Dean off and glanced up at Grace who was practically bouncing up and down. 

“Pleasemommypleasepleaseplease?”

“I’ll see what we can do, okay?” Grace practically tackled you on the couch and then bolted out room. 

Later that night when you went to check on Grace before bedtime, you paused in the doorway when you heard her singing softly. “Jingle bells, Batman smells, Robin laid an egg. The Batmobile lost its wheel, and the Joker got away.” You lost it. 


	15. So, you won’t be home for Christmas?

**Summary for the Chapter:**

> The boys are already away on a hunt when Dean notifies you that they are planning to take on another case.

**Notes for the Chapter:**

> Day 15 - “It’s been a hard year, but now it’s Christmas, and I want to spend it with you.”

Dean Winchester never used to care about Christmas or any holiday in fact. The only time Sam and Dean celebrated properly, Dean had sold his soul and only had a year left. That was until you came along. He still had the same reservations about the holidays but you made them bearable even if you were too enthusiastic about Christmas.

_> > How’s everything going?_

_< < This kid is using my ribs for a punching bag and it hurts. Not to mention all pee breaks I have to take. _

_> > Want me to call later and see if we can’t sooth the beast inside?_

_< < That’s our child you’re talking about and I know you’re busy. It’s fine. I might go bug mom later. Thanks for calling her by the way._

_> > I know with the three of us gone, you would’ve tried to do everything yourself. The doctor told you slow down. _

_< < I should call you Dean Nagchester. I’m resting, I swear._

_> > Pics or it didn’t happen._

_< < I hate you. _

_> > No you don’t. You love me, and you know it._

\--

It had been over a week and there had been no word from Dean. No phone calls or texts but you kept sending pictures. Pictures of how the bunker was coming along with decorations, a few of you and your mom, and a couple of your baby bump. “Mom, he’s okay right?” 

“They say no news is good news, but you’re right it’s kind of weird he hasn’t sent anything.” 

“I really thought they’d be back by now.” You absentmindedly rubbed your baby bump and jumped when you heard your mom’s phone go off. 

“Calm down, Y/N, it’s not good for the baby.” You watched her type and send out the text, and she laughed when you asked who it was. “It was your sister, she was asking where I put Hilda’s food.”

“Hilda?” You raised an eyebrow and tilted your head to the side. 

You watched her pull up a picture of two baby bats and you aww’d at them. “Hilda is the bigger one, and Zelda is white one.” 

“New pets?”

“Early Christmas gift from grandma. She said something about her and grandpa going on a trip… “

“An actually trip or a _hunting trip_?” 

_> > We caught wind of another case._

_< < Didn’t you just finish one? _

_> > This case is just a state over, so we figured we could just knock it out. _

_< < So, you won’t be home for Christmas?_

_> > The way it’s looking, we won’t. _

Dean didn’t have to see your face to know how disappointed you were. He wanted nothing more than be at the bunker with you watching some Christmas movie. Instead he was a state away with Sam hunting a crocotta. 

“Dean, wake the fuck up.” Sam waited for a minute but Dean didn’t budge. He sighed and grabbed the keys for Baby. If Dean wouldn’t budge, Sam figured he could make a food run and make a few phone calls without his brother overhearing.

Dean was jostled awake by his phone ringing. He didn’t recognize the number that was calling him but after the third or fourth time, Dean lost count, he threw the blanket back and answered his phone. “Dean Winchester?”

“Yeah, who the hell is this?”

“You don’t know me -”

“No shit..”

“Sam said you’d be bitchy if I called but my partner and I are taking over your case. You of all people know what happens to hunters if your head isn’t in the game.” 

“I don’t know what to say.”

“Well usually when someone does something nice, you tell them thank you.”

“Well stranger, thank you. I don’t know what I’ll do to repay you but I owe you one.”

“Kayla, that’s my name. See now we’re not strangers. Merry Christmas Dean.”

“Merry Christmas to you too Kayla.” Dean threw his phone on the bed and scrubbed at his face. He looked around the motel room and Sam was nowhere to be found. In this rare moment of silence, he decided to take a shower and clean up. It’d be cutting it close but they’d be able to spend Christmas with you. 

\--

What woke you up wasn’t the urgent need to use the bathroom, it was someone blaring Trans Siberian Orchestra through the bunker. You carefully got up, and shrugged on your house robe and slippers, before wandering the halls. Your eyes finally focused and you spotted a note sitting on top of a medium sized box that was wrapped up. You carefully unfolded it and about cried when you spotted Dean’s messy handwriting. 

‘Y/N, Merry Christmas. By now you’re probably wondering what’s in the box… I’ll give you a minute because I know that made you think of me. We good? Okay, I asked your mom to leave this present out because this one is special. I don’t say it often, but I love you and I know it’s been a hard year. I don’t regret anything and I can’t wait until our lovely baby girl is born. Cas might’ve ruined the surprise but I know I would’ve loved our baby regardless of what the gender was. It’s Christmas, and I can’t to spend it with you. - Love, Dean’

You sat the note aside, and pulled the box closer to you. You slowly unwrapped the box, setting the discarded paper off to the side. You carefully cut along the tape on top of the box and opened it to find it completely empty. “Dean, what the hell…”

“I had to distract you somehow, sweetheart.” 


	16. That time Dean ruined your cookies

**Notes for the Chapter:**

> Day 16 - “You’re going to make me burn the cookies.” Implied smut in this chapter.

You were running out of room to place anything in the kitchen. Looking back, you might’ve gone overboard but it was worth it. **  
**

You were making gift boxes filled with a variety of baked goods for your family and you had just put your latest batch of cookies in the oven when Dean wandered in. “It smells so good in here.” 

“I made mini pies earlier, and now I’m working on the cookies. We have chocolate chip, peanut butter, snickerdoodles, sugar cookies with and without icing, and the gingerbread men are in the oven right now. Is that too much?” 

Dean was laser focused on the mini pies, so you did the only thing you could think to stop him. You smacked his ass. “Hey, I need all of those…”

“Y/N/N?”

You gulped when Dean turned around and the look in his green eyes made you quake. “Yes, Dean?”

“If you wanna play, we’ll play but your ass is in trouble.”

You narrowed your eyes as he slowly started approaching you. “We don’t have time for this Dean.”

“Make time.” He practically growled the sentence out.

\--

“I’m never going to hear the end of this.” You slipped your shirt and panties back on and checked the oven. Sure enough, the two sheets of gingerbread men were burnt. “Dean, you’re helping me remake these. I mean you’re the reason they got burnt in the first place.”

“Worth it though.” Dean muttered as you helped him up. You had him wash his hands first before he started helping you cut out another batch of cookies.

“Good god, put your clothes on Dean!”


	17. Sammy The Red Nosed Reindeer

**Summary for the Chapter:**

> Reader has a talk with Dean about why she’s feeling crummy.

**Notes for the Chapter:**

> Day 17 - Reindeer (antlers, red nose, etc)

“Your daughter is demanding we take a family photo dressed as reindeer.” Dean folded his arms and flopped down in the recliner beside you. **  
**

You raised an eyebrow and paused the movie your were watching to turn and look at him. “Oh, you’re serious… Where did she even get the idea?”

“Sam, where else. She asked me if we could go out and buy the antlers.”

“You told her no right?” Dean dangled Baby’s keys in front of you and you sighed. Dean could never say no to his baby girl. “We could’ve made them together.”

“Hey, what's wrong? You’re grumpier than usual.” Dean picked you up from your chair, took a seat and placed you on his lap. “You can talk to me, you know?”

“I know.”

“Well, are you gonna talk or are we just gonna sit here in silence?” 

“This time of year can rough for me. Some years I’m fine but others well…” Your voice was soft but Dean’s expression shifted into concern. “You know my mom told me when I was older that it was a wraith that got my dad. With Bobby’s help, they were able to track it down and kill it. Dean, what if - what something like that happens to us? Who’s gonna be there to explain to Grace why mommy and daddy aren’t around?” 

“I won’t let it happen.” You shifted so that you could cuddle into Dean’s chest and he was rubbing your back gently. He watched you as you fell asleep with a smile. Dean kissed your forehead and soon found himself asleep.

“Daddy, are we going to -” Grace stopped in the doorway and backed out slowly. She ran down the hallway to her room and with blanket in hand, marched back down to where the two of you were and covered you with the blanket.

Dean would later wake up to two Polaroids laying on the stand next to him. One of you and him sleeping, and one of Sam with a red nose and reindeer antlers.


	18. Be my boyfriend for the day

**Summary for the Chapter:**

> You ask Dean to be your fake boyfriend while the three of you visit your mom.

**Notes for the Chapter:**

> This is Day 18 - Fake dating because the family keeps asking about a significant other and this fills the Fake Dating/Marriage square on my SPN Genre Bingo Card.

“Dean, how much would I owe you if I asked you to do a favor for me?” You tucked your cell between your ear and shoulder as you pulled into the garage. You turned the engine off and sighed.

“It depends on the favor to be honest…” Dean listened as your car door shut and you made your way half asleep down the hallway towards the room that the two of you shared on occasion. At this point in your relationship, you liked Dean and he liked you but the two of you had yet to define what the relationship was.

You smiled as you dropped your duffel next to the bed and hung up your phone as soon as you saw him. “I need you to go with me to my mom’s and pretend to be my boyfriend.”

“Let me think about it, okay?” You fell asleep as soon as your body touched the bed and Dean sighed. What was he going to do? 

\--

“I thought about it last night as you were sleeping. I weighed all of my options and I’ll do it. You however, owe me big time.” You placed your tea cup on the counter and made your way over to where Dean was standing in the doorway.

“I’ll do anything you want Dean.” 

“Don’t say something like that Y/N.”

“Why would I say something I don’t mean?” You grabbed Dean by the collar of his flannel and pressed your lips to his. “I make good on my promises Winchester, don’t you forget it.”

Dean’s eyes went wide with shock and then you heard him laugh. He pecked your lips before pulling you closer and hugging you. “So when do we leave?”

Dean’s grip loosened after you pulled your cell out of your pocket and looked over the details once again. “This afternoon. We’ll be there until after Christmas, I hope that’s okay.” You locked your phone and then it hit you. “Oh shit…”

“What’s wrong?”

“Mom wants to meet Sam too.”

“I’ve always wanted to ask this but,” Dean paused for a second as if he was thinking about how he should phrase his next question. “Where did you grow up?”

“Sioux Falls. We lived about half an hour away from our Uncle Bobby.”

\--

The cabin your family lived in was half an hour away and Dean insisted that he drive. You rolled your eyes and quietly sang along to whatever classic rock song was playing on the radio as the boys talked. Occasionally you chimed in, but for the most part, you stayed quiet. You were trying to work it out in your head how to explain the relationship you had with Dean. 

_ >> Are you guys close? _

_ << Getting closer. Oh, I see Mrs. Frizz went all out this year. _

_ >> It’s worse during the night. I swear, she could land a plane with all the lights she has. _

_ << Oh my god, Mr. Willis decorated the front of his house to look like Nakatomi Plaza… Color me impressed. _

_ >> How do you know that? _

_ << Dean lol _

_ << Oh hey we just pulled up. Please, don’t freak out when I introduce you to the boys. Please? _

_ >> I make no promises…  _

“There she is, home sweet home.” You smiled at the cabin front of you. “Before the two of you ask, this isn’t the house I grew up in but it’s still special. This cabin was where my grandma and grandpa got married - Grandpa’s dad actually built it and he renovated it over time. Once dad passed away, he signed it over to mom.”

“Are your grandparents still alive?” Dean asked out of curiosity and Sam whacked him in the shoulder.

“It’s been a year since I’ve seen them but yeah.”

“Grandma sends her love but they went down south for a hunt.” You smiled as your mom pulled you into her arms for a hug. You smiled and glanced over her shoulder and Harley was standing in the doorway with a huge grin on her face. 

“Mom, you’re embarrassing her in front of her boyfriend, let her go.” Harley winked at you and you rolled your eyes. She was the only one in your family that actually knew what was going on between you and Dean. She looked over both of the boys and her expression turned serious.

“Everything okay Har?” Harley looked at Dean with a bitch face that put Sam’s to shame.

“You look familiar.”

“This is my first time meeting you though.” 

“Dean, this is my mom Jubilee.” She waved with an amused expression on her face as you pulled away. “And the scowling girl behind her is Harley, my younger sister.”

“Nice to meet you.” You chuckled to yourself as the boys and your mom carried your bags inside and you pulled Harley off to the side of the house. 

“I know I’ve seen him before, but where?” You shook your head and took a seat next to her on the porch step. “What’s his last name again?”

“Dean’s? It’s Winchester.”

“This is going to bother me until I figure it out.”

“I know it will. Can we head inside now?” You rubbed your hands up and down your arms as you stared at your sister.

“Heaven forbid you be away from your boyfriend for a few minutes.” She playfully pushed your shoulder and laughed. “We better get in there before mom busts out the photo album and embarrasses you.”

“Great, it’ll be three against one here. Oh, before I forget - his brother’s name is Sam.”

\--

“Y/N.” You felt someone shaking you but all you did was flip over and try to ignore them. “Y/N, come on, please wake up. I have a cup of hot chocolate here with your name on it. It’s made the way you like.” 

“No, let me sleep.”

“It’s almost noon, come on wake up.”

“Dean?” You mumbled into your pillow and heard him chuckle at your response.

“Care to repeat that?” He watched as you sat up and looked over at him. 

“I said we're dating, but I swear Dean, if you try to grab my butt again .. ."

“I would never.” He crossed an x over his chest and drew a halo above his head and you snorted into your cup. 

“You’re welcome to grab my butt anytime though…”

“Same applies to you.” He winked and you chuckled. “Your mom saved you some breakfast and left it up to me to deliver it to you.” He stood up and walked across the room to where a tray was sitting on top of the dresser. He picked it up by the handles and placed it over your lap.

“Mom went all out, wow.” 

“Your sister wanted me to tell you that she made the french toast, your mom made the bacon, and Sam made the fruit salad.”

“And yet, they stuck you with the hardest job of all - waking me up and making sure I eat.”

“It’s all apart of being your boyfriend.”

“I hate to tell you this but Harley knows that we’re not actually dating. I mean, unless you want to tell her otherwise…”

“No, no we just need to keep your mom from finding out.”

“So you need to play nice with Harley, okay?

“ _ Fine.” _

“Y/N, Dean, stop canoodling and come down here!” You heard your mom call from downstairs. 

“We’ll be right down, geez.” 

\--

You heard your mom quietly talking on the phone as you and Dean descended the stairs and made your way into the den where Harley was sitting with Jeffrey on her knee. “Yeah, it's fine if you stop by later. We have guests but they won't mind. You don't have to bring anything if you don't want to, we have plenty. Yeah, yeah I know. I don't want anything to happen to my favorite grumpy old man, be safe and I'll see you later.”

“Why does it sound like mom has a boyfriend?”

“She does but she's just saying he's her friend.” Harley rolled her eyes playfully and you bit back a laugh as your mom glared at her.

“Your dad had quite the collection of books, Y/N.” You smiled as Sam took a seat in the chair across from Harley. 

“You should see his weapon collection in the shed out back. We're lucky no one has asked to see the permits for half of the stuff we have.”

“Okay, this is something I’ve been curious about for a while. How many pets do you guys actually have?” The three of you chuckled as Harley moved Jeffrey from his resting place to her hands and made a follow me motion.

“I have an albino rat named Crowley…” You started to say but paused when you heard someone knocking on the door. “You guys go ahead, I got this.” 

Opening the door, you smiled at the older man who was carrying a handful of gift bags. “Uncle Bobby, oh wow, come in.” You stepped back, allowing him in but he handed you the bags and went back out to his truck. You giggled quietly as he trudged up the driveway with a few more bags.

“Came prepared didn’t you?” 

“I know your mom told me I didn’t have to bring anything, but that’s not who I am. I got a few bags of extra food and some presents for you guys..”

“Aww you didn’t have to do that.”

“I know.” He nudged your shoulder and you fell into the doorway. 

“Y/N!”

“Bobby?” You heard Dean’s voice from down the hall with a look of confusion on his face. “What are you doin’ here?”

“Trixie wanted me to deliver a message and I always stop by..”

“Trixie sounds like a prostitutes name.”

You elbowed Dean in side. “That’s my grandma you’re talking about.”

“Okay, ow sorry.”

“Harley, I got you those mini danishes you like, and there’s something in there for Jeffrey.”

“How often do you stop by?” Dean watched as your sister kissed Bobby on the cheek with a grin. She took the bags from his hand and disappeared into the kitchen. “Better yet, how do you know Y/N and her family?’

“August was a fairly decent hunter, a little on the clumsy side like Garth but his heart was in the right place. I met the girls the night he passed away.”

“Wait, Bobby were the boys ever at your house the same time we were there?” Harley asked from the kitchen. “Because I have this vague memory of watching a little boy work on one of the cars in your salvage yard.”

“That was me.” Dean cleared his throat and you looked over at him. “Sammy was stuck inside because he had a cold that day. I knew someone was watching me but I could never figure out who.”

\--

_ Why did I let you talk me into this?  _

_ I would’ve been fine spending Christmas at the Bunker with you and Sammy. There was no way I could say no you though. “No sweetheart, I’m fine, I promise. Go spend some time with your sister. I’ll be fine.” It’s the little things that you do that turn me into mush. Who knew that one person could change me this much? I’ve been considering asking you to be my girlfriend for a while now but there’s never a good time. I just, I just want to be with you, is that asking too much? God, for someone who claims to hate chick flick moments, I seem to have a lot of them.  _

“Dean? We’re gonna open presents now.” He nods knowing that there’s something special tucked away in his duffel for you. Dean watches from his seat on the couch as you pass the presents out.  _ “We used to alternate who passed out the presents each every year. Apparently, it’s my turn this year.”  _ You grumbled about it but Dean knew you were happy about the whole thing. You sit back down with a couple gifts for yourself and Dean, and smile. “These are from my mom and Harley…” You get as close as you can to his side and whisper something into his ear. 

“You wanna share with the rest of the class or is this something between the two of you?” You heard Sam sass as you jumped away with a blush growing on your face.

“It’s none of your business Samantha.”

“Ow, with the name calling. I guess you don’t want your present from me then…” You rolled your eyes as Sam held up a small sized gift. He tossed it your way and when you unwrapped it, you immediately looked at him with your face on fire.

“Really Sam?” You heard his laughter from across the room and threw a ball of wrapping paper at him.

“What’d he give you that has you blushing so hard?” Your mom asked in genuine concern and when you flashed her the box of condoms, she started laughing. “Just. Just open your gift, you’ll understand.”

“I’m afraid to now.” 

“Just do it, Y/N.” You huffed and picked up the gift that was from your sister. You carefully unwrapped it. 

“I can’t believe you.” In the box in front of you was a set of of Christmas inspired lingerie, and a vibrator. 

“Now you’ll have something to wear for Dean when you wanna feel sexy.” Harley winked at Dean as she handed you another box from your mom. “You can use the other when Dean’s not home, or you can use it together.”

“Why are you the way you are?” You asked quietly and Dean chuckled to himself. Dean was slowly unwrapping a gift from your sister when you heard Bobby call your name.

Bobby handed you a small gift box tied together with ribbon and told you to go ahead and open it. You raised your eyebrow and didn’t question it. You carefully removed the ribbon and sat the lid aside to see a set of keys. “There’s no one I trust more with my car than you, and since you have good ole boyfriend Dean here, he can help you out if something goes wrong with her.”

“Bobby, did you name your car?”

“Why would I do that? Only idjits name their cars.” His face was slightly pink and you heard Dean shout out that Baby was special. 

“I promise, I’ll take good care of her.” 

\--

It all happens in a matter of minutes but Dean gets up from the couch and wanders into the kitchen. You hear cabinets being slammed and Dean’s cursing. “Son of a bitch, where do you keep the booze in this house?” A few more cabinets are slammed open and shut as you excuse yourself. 

“What is your problem?” Dean takes a swig from the bottle he found and stares at you.

“It’s nothing, Y/N. Leave me alone.”

“Doesn’t seem like nothing.” You mutter to yourself as Dean glares at you. “You want me to leave you alone, I will.” 

“Awesome.” He takes another drink and you stomp out of the kitchen. You’re pissed but you wave it off as you walk by your mom, sister and Bobby. 

“What in god’s name is wrong with you boy?” He heard Bobby say from the kitchen doorway. “I don’t know what crawled up your ass and died, but you can’t treat someone like that. That girl has real feelings for you and you wanna slam cabinets because off what? Because I gave her my car? She deserves better.”

“I know that.”

“Get your head out of your ass then and go apologize.”

“Yes sir.”

\--

“Y/N, can I come in?” Dean gently knocks on the bedroom door but when he doesn’t hear your reply, he sighs and sits with his back towards the door. “You don’t have to forgive me for acting like a jackass, I already got lectured by Bobby and he said I don’t deserve you. Maybe he’s right. In this life, it’s hard getting close to anyone but here we are. We’re friends but there’s something more and I want to be more. I do. I’m scared Y/N, I’m scared of losing you. That’s why…”

You opened the bedroom door slowly and Dean fell backwards into the room. “Why did you get so pissed about Bobby giving me his car then?” 

“It’s dumb.”

“Tell me, please?”

“It just means you’ll be able to stuff on your own and won’t need me to drive you around anymore.”

“Yep, you’re dumb.” You snort as you try to help Dean sit upright. “You honestly think I’d give up taking a ride in the Impala just because I have my own car? Look, I love that Chevelle but Baby will always have a special place in my heart.”

“Just like the guy who owns it, right?”

“You’re something else you know that right? Yes, you dumb squirrel.”

“No need for name calling.” Dean finally stood up and made his way into the room. You watched as he made his way over to his duffel bag and pulled out a red baggy. “I got you something… for Christmas I mean. I know it’s not much but as soon as I saw it, it made me think of you.” 

You watch as Dean pulls open the gift bag and pulls out a red and silver bracelet. “Holy shit Dean, that’s gorgeous.” He asks you to hold out your hand and clasps the bracelet onto your wrist. “I love it so much.” 

“What would you think about making our fake relationship a real one?”

“I’d like nothing better.”

“Y/N?”

“Yes Dean?”

“Did you get me anything for Christmas?”

“Nope.” You snort out a laugh and watch Dean’s face shift from happy to offended in seconds. “I’m kidding, it’s nothing huge but I found it at a thrift shop and had to get it for you.” 

“Do I get any hints?”

“Nope.”

“Fine…” His eyes practically bug out when he finally unwraps your gift. “It’s a miniature Baby! This is going on my shelf when we get home.”

“I can’t wait.”


	19. I thought you said Krampus doesn’t exist

**Summary for the Chapter:**

> Grace asks how you met Dean.

**Notes for the Chapter:**

> This takes place around episode 3.8 Also this is for Day 20 - “If I hear one more Christmas song, I’m going to shoot myself.

You were still wide awake watching a movie when Grace suddenly appeared at the side of your bed. “Mommy, I had a nightmare, can I sleep with you you?” **  
**

“Of course you can Gracey.” You threw your blanket back as Grace crawled in beside you. You paused what you were watching as Grace curled up beside you.“Wanna talk about what happened in your dream?”

“Not really.” Just like Dean you thought to yourself and chuckled as Grace looked up at you.

“Mommy, will you tell me the story about how you and dad met?”

–

There had been something strange happening to the residents of Ypsilanti, Michigan. Your grandparents ran a diner in the area, so you took it upon yourself to go help out. Trixie picked you up from the bus station and hugged you as soon as you stepped off of the bus. “It’s so nice to see you dear.” She looked behind you as if she was looking for someone else and you explained that your mom and sister were busy with another hunt. 

“Thanks grandma, how’s grandpa doing?”

“As ornery as ever. He wants you to try out some of the things he’s developed for the diner.” As if on cue, your stomach growled and she chuckled. “Well, we better get you fed.” 

“I can’t wait.”

“There is one catch though, you have to eat in costume.” You raised an eyebrow but just nodded in agreement. You knew better than to argue. 

–

“Oh thank god, this diner isn’t playing Christmas music.”

“Dean..”

“I’m serious, Sam. If I hear one more Christmas song, I’m going to shoot myself.” You had to hold your hand over your mouth to keep a laugh from escaping. Even though they owned a Christmas themed diner, they wanted everything to be normal. So your grandpa had a jukebox installed with a variety of music. You were currently bobbing your head to the song that was playing. 

Dean was watching the back of your head carefully. “Sam, please tell me your seeing the same thing I am.”

“Girl with horns in the booth in front of us, yes. I was going to say something, but I didn’t want to be rude.” 

He gave his order to the waitress, and as she walked away, Dean excused himself. He passed your booth and he paused before going into the bathroom. You were currently eating some form of pie with a grin on your face. You had a notebook open and would occasionally write something down. He watched you for a second more and then Dean pulled out his phone and dialed Bobby’s number. He waited until he was in the bathroom to connect the call. “What do you want now? I thought the case was wrapped up.”

“I thought you said Krampus didn’t exist.” 

“He doesn’t.” Dean opened the door a crack and managed to take a picture of you as you were sitting in your booth. He sent it to Bobby’s phone and there was silence for a couple of minutes. “That’s obviously a costume boy…”

“How do you know?”

“Is that diner run by an elderly couple?”

“Yes… how the hell do you know that?”

“They’re hunters, you idjit. That girl is their granddaughter Y/N.”

“Oh.”

–

“So did daddy ever introduce himself to you?” 

“Eventually he did.” You chuckled as Grace flipped on her back. 

“I can’t believe daddy thought you were a demon.” Grace asked with a quiet yawn. . 

“To be fair, that costume was pretty convincing.” You heard Dean from the doorway and Grace perked up.

“Welcome home daddy.” Dean kissed Grace’s forehead and tucked her in. He removed his boots, his flannel and his jeans, as he crawled in bed beside her. “Mommy, so does Krampus actually exist?”

“I don’t actually know baby.”

“Bobby would tell you no and that your an idiot if you believing otherwise.”

“Well if he doesn’t exist, what’s he like?” 

“According to the lore, Krampus originated in Germany. He’s sort of like the anti-Santa Claus. Instead of leaving coal for all the naughty children, he would beat the kids with whips and chains, and then stuff them into the basket he carries on his back.”

“So if I’m bad mommy will beat me with chains and stuff me in a basket?”

“Dean, if you answer this incorrectly, I will f-udging kill you.”

“Daddy run, mommy’s gonna whip you with chains!”

“Daddy might like that a little too much.” You watched as Dean’s face shifted into an expression you’ve never seen before. If Grace wasn’t in your bed, you knew you’d be in trouble.


	20. The hot chocolate on your breath says otherwise

**Summary for the Chapter:**

> Dean tries to make a bet with you but you have other plans.

**Notes for the Chapter:**

> Day 20 - Hot Cocoa Kisses

“Sammy’s out on a hunt, Grace is with your parents - it feels weird to say that Bobby is going to be my father-in-law but we have the bunker to ourselves. **So….. you wanna….hot chocolate and chill?** ” Dean waggled his eyebrows and you hit him with a pillow as you laughed. 

**“If you ask me that one more time, I will dump hot chocolate on you.”**

“You wouldn’t dare.” 

“I don’t think you want to test that now do you?” Your smile faltered as Dean’s fingers ghost down your side. “Fine, I won’t do it.” 

“Hey Y/N, how many kisses do you think you could fit in your mouth?”

You stared at the bowl of mixed Hershey Kisses on your dresser and shrugged. Dean’s eyes twinkled with mischief as he got up from his spot on the bed and brought it over to where the two of you were sitting. “Wanna make a wager?”

“First things first Winchester.” You pulled his face closer and peck him on the lips. You kiss

him again as your eyes narrow. “Were you trying to cheat?”

“No.”

“The hot chocolate on your breath says otherwise.”

“Fine, I wanted go see the lights with you.”

“Wait, there’s was a catch to that, wasn’t there?” You watch Dean’s face carefully. “What the loser has to drive and the passenger gets to play all they want… Oh Dean. If you wanted to play, all you had to do was say so.”

“I really do want to go light watching with you though.”

“We will.” You pushed Dean on the chest with enough force that his legs hit the bed frame. “After I rock your world that is.”


	21. Tis the season to be awesome.

**Summary for the Chapter:**

> Dean takes care of you while you're sick.

**Notes for the Chapter:**

> Day 21 - 'Tis the season?

“Is mommy gonna be okay?” Grace asked from the doorway with her stuffed platypus in hand. **  
**

“Of course she is. Mommy just has a very nasty cold and daddy is gonna take care of her.” Dean brushed Grace’s bangs back and kissed her forehead. 

“Is that why Uncle Sam is staying away? ‘cause he doesn’t want to get sick..”

“You should go stay with him. I don’t want you catching what I have.”

“Won’t daddy catch it?” She tilted her head like Cas and you started laughing which eventually turned into a coughing fit.

“I won’t get sick.” Dean winked at you as you tried catching your breath and Grace stared over at the bed. “You wanna know why?”

“Why?”

“Daddy’s awesome, and I rarely get sick.”

“Famous last words.” You muttered as Grace giggled.

“You know what they say 'tis the season to be awesome.”  
  
“No one says that.” 


	22. You’re the cutest angel that I’ve ever seen.

**Summary for the Chapter:**

> Grace wants you to make a costume for her school pageant but a snow storm coming puts a damper on plans.

**Notes for the Chapter:**

> Day 22 - You’re just cute enough to be the tree topper.

You lucked out when Grace told you she needed a costume for her school play. The two of you were looking at the list of options that her teacher sent home and you almost cackled when you Grace pointed to an angel. “Please mommy?” **  
**

“You know that real angels look nothing like these costumes, right?”

“Yeah, Uncle Cas told me, but those stories make me feel sad.”

“We all miss Uncle Gabe. Well, daddy doesn’t but that’s because…”

“Uncle Gabe killed him over and over.” Grace frowned as she climbed up on your lap and you brushed her hair away from her face. She had her arms wrapped around your neck and her head was tucked into your shoulder. You made a mental note to talk to Cas about the stories he was telling her.

“We don’t talk about that while Uncle Sammy is present or play Heat of The Moment, unless we know he’s not here.” 

“Mommy, since we don’t have school tomorrow, can we take a trip into town to get what we need for my costume?” 

“Do you want a new dress, or do you want me to make it?”

“You can make my dress?” Her green eyes lit up and you chuckled.

“Of course. I’ll talk to daddy and maybe tomorrow we can have a family day. Would you like that?”

“Can Uncle Sam come too?”

“If he wants to.”

–  
  


“Mommy, daddy wants to talk to you.” You heard her tell Dean that she loves him and that she hopes she can see him later. Grace hands you your cell phone with a smile as she takes off down the hall towards her room. 

“Thank you baby.” You shake your head as you bring your cell phone up to your ear. “Hey babe, what’s up?”

“I know Gracey was looking forward to seeing everyone but there’s a massive snow storm moving in. Sam and I are about an hour away but her teacher called and said that they’re postponing the pageant until it passes.”

“She’s been wearing her angel costume all afternoon.” You were leaning in the doorway and sighed. “I told her not to spill anything on it, but Dean she’s so adorable.”

“I hope you took a picture for me.” The two of you chuckled and you heard Sam in the background. “Yeah, I know. We’re gonna stop by the grocery store and pick up what we can before we head home. Hopefully it’s not too packed.”

“You two be safe, and I’ll see you when get here, okay?”

“We’ll be safe. Y/N, I love you.” You heard Sam making smoochy noises and you rolled your eyes. 

“I love you too Dean.”

–

“My mommy made my costume, isn’t it pretty?” She did a spin and giggled. 

“You’re the cutest angel that I’ve ever seen. Next to me that is.” Gabriel chuckled with a wink as the younger girl looked at him confused. “Uncle Cas has been telling you stories, huh?”

“I gots a question for you Unca Gabe…” Gabe for the first time in his life didn’t know how to answer her. He had his reasons for doing what he did but how could he explain that to a four year old?

“Oh sweetpea, what I did to your dad in the past…” He paused and was ready to snap out of Grace’s room when he heard your footsteps coming down the hall, but he decided against it. 

“Grace, you’re pageant has been….” You looked over and saw him standing by the closet and the son of a bitch waved. “Gabe?”

“How’s it going sweet cheeks?” Grace looked between the two of you and tugged on your hand. 

“Don’t be mad at him, mommy.” 

“I could never be mad at him, sweetheart. I’m just confused and a little upset. Dean told me you died…”

“Of course he did.” Gabe rolled his eyes and uncrossed his arms. “I’m not here for him, I’m here because this cute little girl in front of me prayed to me.”

“That doesn’t sound creepy at all.” You chuckled as Gabe swatted at you and Grace went back to playing. “Okay, now back to what I originally came in here for. Grace, your teacher called and said they had to postpone your pageant tonight. We’re supposed to get a pretty bad snowstorm.”

“I don’t get to be an angel tonight?”

“Kid, take it from someone who knows, you’re just cute enough to be the tree topper.”

“Gabe, stop trying to impress my 4 year old, she already thinks the world of you.”

“Who wouldn’t?” He winked at the two of you and then disappeared.


	23. Come sit down and open this

**Summary for the Chapter:**

> Dean and Grace make up a present for you.

**Notes for the Chapter:**

> Day 23 - Fireplace and this fills the Shark Week square I have for SPN Fluff Bingo

“Daddy, I think something’s wrong with mommy.” Dean looked up from the magazine he was flipping through and quickly hid it under a stack of books that was next to him. **  
**

“Why, did she say something?” 

“I heard her cursing out Chuck, whoever that is, for making her a woman.” Dean chuckled as Grace stared up at him. “Can’t we help her out?”

“Gracey, you wanna help daddy out with something?” Grace was nodding her head so fast that Dean thought it was going to fly away. “Let me text uncle Sammy, and then we’ll go to the store.”

“O’tay!”

–

You had to get up and use the bathroom. There was just one problem, you didn’t want to move. Sighing, you pulled out a new pair of underwear and pajama pants, just incase and made your way towards the bathroom. You took care of business and brushed your teeth. A few minutes passed and you threw your dirty clothes in the laundry basket. You were lucky that it wasn’t a heavy day, so everything was safe. You checked your phone that was charging on the nightstand. There were no calls but one text from Sam letting you know that Dean and Grace went to the store.

“Okay, ow shit..” You clutched your lower stomach as a wave of cramps rolled in. “Where did I put it?” You’d have to ask Dean where the heating pad was when he got back. Until then, you wrapped yourself in your coziest blanket and fell asleep. 

“Y/N.” You hummed in response but yet your eyes were still closed. “Babe, wake up. I have a surprise for you.” You slowly sat up and rubbed the sleep from your eyes and peered up to see Dean standing near you with a cup of warm tea and some pain pills. “Here, how was it today?” You took one pill at a time, savoring the warmth that came from the tea.

“It wasn’t that bad, cramps kicked my ass but at least I didn’t bleed through.” Dean leaned forward to kiss you softly. “Now what was this about a surprise?”

“Go use the bathroom and I’ll go get your gift.” He winked as he left the room and you made your way towards the bathroom. You changed your pad and washed your hands. By the time you came back out, Dean had changed into a blue plaid pajama pants and a gray henley. He was lounging on his side of the bed with a box sitting beside him. “Come sit down and open this!”

“You are way too excited about this.” You muttered as you took a seat next to him. You removed the lid and on the inside was a new set of Christmas pajamas, some gummies, a small bag of chocolates and Love Actually. 

“You don’t like chick flicks Dean.”

“Don’t quote me to me okay.” You quietly chuckled as he popped the DVD in and loaded up the movie. 

“Any more surprises I should know about?”

“Unless you can magically make a fireplace appear of thin air, nope.” 

“I can’t but -”

“No.”

“Okay, second best thing. Hand me my laptop. I’ll pull up a video of the yule log and we can pretend we’re cuddling in front of it.” 

“Shark week is the worst.” You heard Dean say quietly as you curled into his side and wrapped his arm around your shoulder and placed his hand on your lower stomach. 

“It is. Now press play.” 


	24. Have you been a good girl?

**Summary for the Chapter:**

> It's Christmas Eve and you finally finished decorating.

**Notes for the Chapter:**

> Day 24 - It’s Christmas Eve, that means I get to open one gift

The bunker was busier than ever. This year, you decided to invite your family to spend the holidays with the four of you. “Dean, come on please? I need help reaching the top of the tree and I know you don’t trust me on a ladder.” 

“If you could go five feet without bumping into an imaginary wall, I wouldn’t be so worried.” Dean heard you grumble as you finished placing the last ornament on the tree. “Hey, come here a second.” You sighed as you took a step back and got a good look at the tree.

“I think we did a good job.” Dean smiled as he laid his hand on your shoulder. You ran your thumb across his knuckle and gently squeezed his hand. You heard someone clear their throat as the two of you turned to look.

“I’m not interrupting anything, am I?” Your mom smiled as she made her way closer into the room and stopped in front of the tree. “Y/N, if your dad were here, I think he’d be jealous of your decorating skills.”

“Well everything I learned, I learned from him.” You smiled as your mom nodded with a sad smile on her face. “Did Grace give you any trouble?”

“She conked out after I read her a few bedtime stories. I think she might be disappointed that she didn’t get to open a gift tonight though..”

“She’ll have plenty to open tomorrow.” 

“She’s our little Christmas baby.”

“Now, I do have to ask - is your tree topper a star or an angel?” 

“A star.” Dean replied with the star topper in hand. He removed his hand from your shoulder and moved over towards the tree. “Y/N, come hold the ladder steady, will ya?” Your mom wished the two of you good night with a wink and made her way towards her room.

“I guess I can.” You sassed and Dean turned to look at you with a grin on his face. 

“Fine, if you don’t want to cooperate, I guess you can open your gifts tomorrow.”

“Not fair…” You pouted as you held the ladder steady for him. “It’s Christmas Eve, that means I get to open one gift.”

“Have you been a good girl, Y/N?”

“Of course I’ve been a good girl.” You whispered as Dean made his way down the ladder. 

“Prove it.”


	25. Wake up, it’s Christmas

**Summary for the Chapter:**

> You celebrate Grace's birthday and Christmas, but when Cas asks an innocent question, you decide on something...

**Notes for the Chapter:**

> The last and final day for these fics. I had so much fun writing this series.

“Grace, baby girl, wake up.” She grumbled and buried herself deeper into the covers. “We’ll have breakfast, and then open presents with grandma, grandpa, Aunt Harley, Uncle Sam, and Uncle Cas.” **  
**

“What about daddy?” You heard her muffled voice through the blanket and chuckled.

“Daddy’s making us a huge breakfast. There’s no way he would miss your special day.” The top of her head poked out from the covers and you smiled, “There’s my birthday girl!”

“Morning mama.” Grace yawned as she rubbed the sleep from her eyes and tried to pat down her sleep tousled hair. “Don’t you wish Grandpa August could be here with us?”

“Oh baby girl, that’s something I’ve wished for since he passed away but I know he’s up there watching over us. He’d love you so much.” You felt Grace crawl into your lap and hug your torso.

“It’ll be okay, mommy.” You blew a raspberry on her cheek and Grace squirmed free. She put on her house slippers and stood at the door, waiting for you. “I’m hungry, let’s go!”

–

The kitchen was busy. Grace practically rushed over go where your mom was sitting and crawled up into her lap. “Happy birthday babygirl, and Merry Christmas. Are you excited to open your presents?”

“Mhmm but mommy said I had to eat breakfast first.”

“Your momma would be right.” She winked over at you as you wrapped your arms around Dean’s waist. “Get a room!”

“You hush.” You stuck your tongue out at your mom and then kissed Dean on the cheek. “Merry Christmas baby.”

“I hope your hungry. We got pancakes, eggs, loads of bacon, sausage, toast, biscuits and gravy and so much more.”

“Mom helped you didn’t she?”

“Said she woke up early and wanted to get a head start on cooking. She has Gracey’s cake and a couple pies in one oven.”

After breakfast, your family spent the morning exchanging presents. Your mom surprised Grace with her birthday cake, and as soon as all of you were done singing happy birthday, she blew out the candles.

“So Grace, what’d you wish for?”

“I can’t tell you what I wished for daddy, it won’t come true then!”

–

“It’s been two years since he has proposed, so why hasn’t Dean made Y/N his wife?”

“Cas, buddy, when have we had time to sit down and plan a wedding? I’ll bet you twenty bucks Y/N doesn’t even have a dress.” You flushed as the two of them looked over at you. “See?”

“I don’t even know where to start to be honest.” Gabe snorted from across the room. “What?”

“Don’t all girls plan their dream wedding when they’re small?”

“You’re confusing me with Harley. I never -”

“Don’t lie to your guardian angel, Y/N. You planned everything.” You face was still warm as Gabriel moved Grace from his lap, and stood up. “Deep down, you always wanted to get married. You never stopped believing in love even though your father, may he rest in peace, passed away.” 

“Okay, I get it. I still don’t have a dress, and we have nothing here for a wedding.” 

“I got you girl.” He winked and you rolled your eyes. “You’re marrying a Winchester, so you’re wearing the perfect thing already.” You looked down at your red and black plaid dress and boots that you were wearing and chuckled. He was right actually. 

“I can marry the two of you, if you don’t want to wait.” Harley spoke up and you looked over at Dean who was grinning widely. 

“You honestly want to do this today?”

“It’s either this or Vegas.”

“My mom would kill me if we eloped, you know that right?” You quietly chuckled and then looked over at Bobby with misty eyes. “Would you… would you walk me down the aisle?”

“I’d be honored to.”

“I love you dad, thank you.” You wiped away the tears that were threatening to fall. “All right people, I guess we’re having a wedding today. What do we need?”

“We can skype your grandparents and they can watch from wherever they are. Other than that, we have all the guests we need right here. Sam, will you be my best man?” 

“Of course.”

“Harley?” 

“I love you but I’m handing my maid of honor crown to the birthday girl.”

“What do you think sweetheart? You wanna be mommy’s maid of honor?”

“Will I get wear to a pretty dress?” 

“The prettiest! Go ask Uncle Gabe for help, he looks like he’s itching to do something.” You winked at Gabe who snapped his fingers and Grace was in an outfit that closely matched yours. The only difference was the white vest with colorful reindeer and the white necklace.

“This is the best birthday ever!” Grace scrambled over to your mom and she tickled Grace’s side. “Don’t you have to find all that stuff?”

“Stuff?” 

“You know…” 

“I think she means the something borrowed, something blue, something old and something new.”

“Yeah! That stuff…” She removed one of her hair barrettes and pressed it into your hands. “Here’s somethin’ blue. What else is there again??”

“Something borrowed, something old and something new.” 

“Y/N, come here for a minute and let me fix your hair and makeup.” Your mom and sister pulled you towards the bathroom so they could work. 

You huffed in protest. “Fine.”

You never argued when Harley asked to style your hair. She taught herself so much and you learned that if you were stressed, all anyone had to do was play with your hair for a bit. You could feel her running the brush through your hair, so you closed your eyes for what felt like a few seconds. It’s not until you feel your mom place her hand on your shoulder that you jerked awake. “Y/N, are you okay?”

“I’m fine… I think anyways.” You felt something cool press against your forehead as your mom and sister continued working. “Thanks Gabe.”

“Not a problem sweet cheeks. I have a bouquet here wrapped in one of Samsquatch’s old flannel shirts. Will that work for something?”

“Something borrowed.” You and Harley replied in unison with a chuckle.

“I’m wearing the bracelet Dean got me for Christmas all those years ago, so that’s something old.” You felt your mom move around you and when you looked down you were wearing a necklace with a snowflake shaped pendant.

“Your father wanted you to have this whenever you got married.”

“Mom….”

“Don’t you dare cry, I just fixed your makeup.”

“Harley has one too, if that’s what you’re worried about. Now,” She handed you the bouquet with a proud smile on her face. “Let’s get you married, shall we?”

–

“Mrs. Winchester, are you asleep?” Dean asked as he kissed your shoulder. He heard you mumble something but you made no effort to open your eyes. “I can work with this.” Dean chuckled to himself as his left arm tightened around your waist. “You looked so beautiful today, and you blew me away with your vows. I love you Y/N, and I can’t wait to spend our life together. I hope that our next kid turns out amazing like Grace did.”

“Well, we have time to make sure that happens.” 

“It will happen again, right?”

“Of course, so Mr. Winchester, you wanna practice making another baby?”

“I thought you’d never ask.”


End file.
